Colored compounds of the seleno-azin series and process of making same.



forms dark needles having a green metallic UNITED era as rarnnr QFEIGE,

PAUL EHRLICH AND HUGO BAUER, 0F FRANKFCRT-ON-THE-MAIN, GERMAN Y, AS- SIGNQRS TOFARBWERKE VORM. MEISTER LUCIUS & BRll'NING, OF HljCHST-0N- THE-MAIN, GERMANY, A CORPORATION OFGERMANY; v

COLORED COMPOUNDS OF THE 'SELENO-AZIN SERIES A ND PROCESS OF MAKING SAME.

- Nonrawing.

- Specification of Letters Patent. Patented Feb 1 7, 191%,

Application filed April 4, 1913. I Serial No. 758,969.

. quently oxidizing the nitro derivatives of the selenoazm:

jTo all whom it may concern Be it known that we, PAUL EHRLIOH, M. I, professorof medicine, and HUGO BAUER, h. D., chemist, citizens of the Empire of gel-many," residing at Frankfort-onthe- I '1 Iain. Germanv. have invented certain new and useful Improvements in Colored Com- I Se pounds of the Seleno-Azin Series and POC- colored substances are obtained, valuable for esses of Making Same, of which the follow- 5 therapeutical purposes. ing is a specification. f the selenoazin can be prepared by treating Our invention relates to themanutacture i ortho-aminoselenophenol with dior triniof compounds of the selenoazin series. lVe tro-halogenbenzene, as indicated by the folhave found that by reducing and subselowing equation:

N02 biog I l I SeH no/\/' noz 1, Am! The new productsobtainabletheretroni by reduction and subsequent oxidation are most probably salts of the amino derivatives of phenazselenonium-hydroxid having the for Example II The dinitrophenoseleno-aziii mentioned inExample I, can be transformed into trinitrophenoseleno-azin by treating it mula: acid The pr oduct IS a red-substance, which N is converted into a dyestufi in the manner I dlescribed in Example I The dyestufi thus 0 tained forms small dark needles having a' I l 11'1 t 1101' t green meta 1c us or, so u e in Water 0 a violet solution. I p 03 Having now described our invention, What They are colored substances, soluble in We claim is:

into amino derivatives of the selenoazin. facturing colored products, being salts of The following examples illustrate our inamino derivatives of phenazselenonium- Vention. hydroxid, which consists in first reducing a Example I: Dinitrophenoselen'o-azin, obtained from picryl chlorid and ortho-aminothen oxidizing the product of reduction.

selenophenol, is treated with 1 calculated As new Products, Salts of i PV Y quantities ofstannous chloridand hydrofi of p s n nlum hydroxrd, being chloric acid, taking care that the tempera- 9 compounds yleld 31111119 t d t exceed +50 (1 B th 1- rivatrves of seleno-azln when treated with a in below this temperature, the double tin q g g l g SOluble 1 .1 Water n safi of the resulting leuco-base separates. g,

dark color and a metallic luster.

, In testimony whereof, We aiiix our signatures in presence of two Witnesses.

PAUL EHRLICH. HUGO BAUER.

Water, which by reduction are transformed I l. The herein-described process of manu- I i l l I I l I l i From the aqueous solution of the said tin salt the tin is precipitated by means of hydrogen sulfid, and from the filtrate from this precipitate the new compound is precipitated by introducing air or, preferably, by adding ferric chlorid. he compound thus obtained is soluble in Water to a greenishbrown solution, and when recrystallized l/Vitnesses CARL GRUND, ELSE Menus.

luster.

Said derivatives of.

when crystallized, needles of a nitro derivative of phenoseleno-azin and 

